In my opinion it would have to be Chris Isaac. I once saw him on 'The Panel' TV show, years ago and they were teasing him about his side burns. Cool as a cucumber he just replies, to the audience, "can any woman here, who does NOT want to sleep with me, please stand up?" They panned across the audience to not a hand raised and he just replied to the guys teasing him, "sorry, what where you saying?" That was pretty cool.
among those who still with us IMO Huey Morgan from "fun loving criminals" He is cool and funny. I use his line "I lived in Peru with the mountain people" for pickup.
Saw them in Melbourne last year, and for a bloke in his 60's he had the crowd going off. It was a great concert and we were glad we made the trip over.
John Cougar Mellencamp also had a certain swagger... saw him many years ago at the old Perth Entertainment Centre and he blew the lid off the place, must have done a six song encore - 4 after the house lights went on, he was just in the zone and enjoying himself so much.